3-(acyloxyphenyl)benzofuran-2-one stabilizers

ABSTRACT

Compounds of the formula (1) ##STR1## in which R 2 , R 3 , R 4  and R 5 , independently of one another, are hydrogen, C 1  -C 25  alkyl, C 7  -C 9  phenylalkyl, unsubstituted or C 1  -C 4  alkyl-substituted phenyl, unsubstituted or C 1  -C 4  -alkly-substituted C 5  -C 8  cycloalkyl; C 1  -C 18  alkoxy, hydroxyl, C 1  -C 25  alkanoyloxy, C 3  -C 25  alkenoyloxy, C 3  -C 25  alkanoyloxy which is interrupted by oxygen, sulfur or &gt;N--R 16  ; C 6  -C 9  cycloalkylcarbonyloxy, benzoyloxy or C 1  -C 12  alkyl-substituted benzoyloxy, where R 16  is hydrogen or C 1  -C 8  alkyl, or, furthermore, the radicals R 2  and R 3  or the radicals R 4  and R 5  together with the carbon atoms to which they are bound form a phenyl ring, R 4  is additionally --(CH 2 ) n  --COR 11 , in which n is 0, 1 or 2, R 11  is hydroxyl, ##EQU1## C 1  -C 18  alkoxy or ##STR2## R 14  and R 15 , independently of one another, are hydrogen or C 1  -C 18  alkyl, M is an r-valent metal cation and r is 1, 2 or 3, R 7 , R 8 , R 9  and R 10 , independently of one another, are hydrogen, C 1  -C 4  alkyl or C 1  -C 4  alkoxy, with the proviso that at least one of the radicals R 7 , R 8 , R 9  and R 10  is hydrogen and, in the case where R 3 , R 5 , R 6 , R 7  and R 10  are hydrogen, R 4  is additionally a radical of the formula (2) ##STR3## in which R 2 , R 8  and R 9  are as defined above and R 1  is as defined below for m=1, and R 12  and R 13 , independently of one another, are hydrogen, C 1  -C 12  alkyl or phenyl, m is 1 or 2, and, in the case where m is 1, R 1  is hydrogen, C 1  -C 25  alkanoyl, C 3  -C 25  alkenoyl, C 3  -C 25  alkanoyl which is interrupted by oxygen, sulfur or &gt;N--R 16  ; C 6  -C 9  cycloalkylcarbonyl, benzoyl or C 1  -C 12  alkyl-substituted benzoyl, R 16  is as defined above and R 6  is hydrogen or a radical of the formula (3) ##STR4## in which R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9  and R 10  are as defined above, and, in the case where m is 2, R 1  is ##STR5## in which R 17  is a direct bond, C 1  -C 18  alkylene, C 2  -C 18  alkylene which is interrupted by oxygen, sulfur or &gt;N--R 16  ; C 2  -C 18  alkenylene, C 2  -C 20  alkylidene, C 7  -C 20  phenylalkylidene, C 5  -C 8  cycloalkylene, C 7  -C 8  bicycloalkylene or phenylene, R 16  is as defined above and R 6  is hydrogen, are described as stabilizers for organic materials against oxidative, thermal or light-induced degradation.

The present invention relates to compositions comprising an organicmaterial, preferably a polymer, and 3-(acyloxyphenyl)benzofuran-2-onesas stabilisers, to the use of the same for the stabilisation of organicmaterials against oxidative, thermal or light-induced degradation and tonovel 3-(acyloxyphenyl)benzofuran-2-ones.

Individual 3-(hydroxyphenyl)benzofuran-2-ones and3-(acetoxyphenyl)benzofuran-2-ones have been described, for example, byM. H. Hubacher, J. Org. Chem. 24, 1949 (1959); J. Gripenberg et al.,Acta Chemica Scandinavica 23, 2583 (1969); M. Auger et al., Bull. Soc.Chim. Fr. 1970, 4024 and J. Morvan et al., Bull. Soc. Chim. Fr. 1979,II,575.

The use of certain benzofuran-2-ones as stabilisers for organic polymersis disclosed, for example, in U.S. Pat. No. 4,325,863; U.S. Pat. No.4,338,244 and EP-A-415 887.

It has now been found that a selected group of such benzofuran-2-ones isparticularly suitable as stabilisers for organic materials sensitive tooxidative, thermal or light-induced degradation.

Accordingly, the present invention relates to compositions comprising

a) an organic material which is subject to oxidative, thermal orlight-induced degradation and

b) at least one compound of the formula (1) ##STR6## in which R₂, R₃, R₄and R₅, independently of one another, are hydrogen, C₁ -C₂₅ alkyl, C₇-C₉ phenylalkyl, unsubstituted or C₁ -C₄ alkyl-substituted phenyl,unsubstituted or C₁ -C₄ alkyl-substituted C₅ -C₈ cycloalkyl; C₁ -C₁₈alkoxy, hydroxyl, C₁ -C₂₅ alkanoyloxy, C₃ -C₂₅ alkenoyloxy, C₃ -C₂₅alkanoyloxy which is interrupted by oxygen, sulfur or >N--R₁₆ ; C₆ -C₉cycloalkylcarbonyloxy, benzoyloxy or C₁ -C₁₂ alkyl-substitutedbenzoyloxy, where R₁₆ is hydrogen or C₁ -C₈ alkyl, or, furthermore, theradicals R₂ and R₃ or the radicals R₄ and R₅ together with the carbonatoms to which they are bound form a phenyl ring, R₄ is additionally--(CH₂)_(n) --COR₁₁, in which n is 0, 1 or 2, R₁₁ is hydroxyl, ##EQU2##C₁ -C₁₈ alkoxy or ##STR7## R₁₄ and R₁₅, independently of one another,are hydrogen or C₁ -C₁₈ alkyl, M is an r-valent metal cation and r is 1,2 or 3, R₇, R₈, R₉ and R₁₀, independently of one another, are hydrogen,C₁ -C₄ alkyl or C₁ -C₄ alkoxy, with the proviso that at least one of theradicals R₇, R₈, R₉ and R₁₀ is hydrogen and, in the case where R₃, R₅,R₆, R₇ and R₁₀ are hydrogen, R₄ is additionally a radical of the formula(2) ##STR8## in which R₂, R₈ and R₉ are as defined above and R₁ is asdefined below for m=1, and R₁₂ and R₁₃, independently of one another,are hydrogen, C₁ -C₁₂ alkyl or phenyl, m is 1 or 2, and,

in the case where m is 1,

R₁ is hydrogen, C₁ -C₂₅ alkanoyl, C₃ -C₂₅ alkenoyl, C₃ -C₂₅ alkanoylwhich is interrupted by oxygen, sulfur or >N--R₁₆ ; C₆ -C₉cycloalkylcarbonyl, benzoyl or C₁ -C₁₂ alkyl-substituted benzoyl, R₁₆ isas defined above and R₆ is hydrogen or a radical of the formula (3)##STR9## in which R₁, R₂, R₃, R₄, R₅, R₇, R₈, R₉ and R₁₀ are as definedabove, and,

in the case where m is 2,

R₁ is ##STR10## in which R₁₇ is a direct bond, C₁ -C₁₈ alkylene, C₂ -C₁₈alkylene which is interrupted by oxygen, sulfur or >N--R₁₆ ; C₂ -C₁₈alkenylene, C₂ -C₂₀ alkylidene, C₇ -C₂₀ phenylalkylidene, C₅ -C₈cycloalkylene, C₇ -C₈ bicycloalkylene or phenylene, R₁₆ is as definedabove and R₆ is hydrogen.

Alkyl of up to 25 carbon atoms is a branched or unbranched radical, forexample methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl,tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl,1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl,1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl,2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl,decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl,tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl,eicosyl or docosyl. One of the preferred meanings of R₂ and R₄ is, forexample, C₁ -C₁₈ alkyl. A particularly preferred meaning of R₄ is C₁ -C₄alkyl.

Examples of C₇ -C₉ phenylalkyl are benzyl, α-methylbenzyl,α,α-dimethylbenzyl and 2-phenylethyl. Benzyl is preferred.

Examples of C₁ -C₄ alkyl-substituted phenyl, which preferably contains 1to 3, in particular 1 or 2, alkyl groups, are o-, m- or p-methylphenyl,2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl,2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl,2-methyl-6-ethylphenyl, 4-tert-butylphenyl, 2-ethylphenyl and2,6-diethylphenyl.

Examples of unsubstituted or C₁ -C₄ alkyl-substituted C₅ -C₈ cycloalkylare cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl,methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl,tert-butylcyclohexyl, cycloheptyl and cyclooctyl. Cyclohexyl andtert-butylcyclohexyl are preferred.

Alkoxy of up to 18 carbon atoms is a branched or unbranched radical, forexample methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy,pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, tetradecyloxy,hexadecyloxy or octadecyloxy.

Alkanoyloxy of up to 25 carbon atoms is a branched or unbranchedradical, for example formyloxy, acetyloxy, propionyloxy, butanoyloxy,pentanoyloxy, hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy,decanoyloxy, undecanoyloxy, dodecanoyloxy, tridecanoyloxy,tetradecanoyloxy, pentadecanoyloxy, hexadecanoyloxy, heptadecanoyloxy,octadecanoyloxy, eicosanoyloxy or docosanoyloxy.

Alkenoyloxy of 3 to 25 carbon atoms is a branched or unbranched radical,for example propenoyloxy, 2-butenoyloxy, 3-butenoyloxy, isobutenoyloxy,n-2,4-pentadienoyloxy, 3-methyl-2-butenoyloxy, n-2-octenoyloxy,n-2-dodecenoyloxy, iso-dodecenoyloxy, oleoyloxy, n-2-octadecenoyloxy orn-4-octadecenoyloxy.

Examples of C₃ -C₂₅ alkanoyloxy which is interrupted by oxygen, sulfuror >N--R₁₆ are CH₃ --O--CH₂ COO--, CH₃ --S--CH₂ COO--, CH₃ --NH--CH₂COO--, CH₃ --N(CH₃)--CH₂ COO--, CH₃ --O--CH₂ CH₂ --O--CH₂ COO--, CH₃--(O--CH₂ CH₂ --)₂ O--CH₂ COO--, CH₃ --(O--CH₂ CH₂ --)₃ O--CH₂ COO-- andCH₃ --(O--CH₂ CH₂ --)₄ O--CH₂ COO--.

Examples of C₆ -C9cycloalkylcarbonyloxy are cyclopentylcarbonyloxy,cyclohexylcarbonyloxy, cycloheptylcarbonyloxy and cyclooctylcarbonyloxy.Cyclohexylcarbonyloxy is preferred.

Examples of C₁ -C₁₂ alkyl-substituted benzoyloxy are o-, m- orp-methylbenzoyloxy, 2,3-dimethylbenzoyloxy, 2,4-dimethylbenzoyloxy,2,5-dimethylbenzoyloxy, 2,6-dimethylbenzoyloxy, 3,4-dimethylbenzoyloxy,3,5-dimethylbenzoyloxy, 2-methyl-6-ethylbenzoyloxy,4-tert-butylbenzoyloxy, 2-ethylbenzoyloxy, 2,4,6-trimethylbenzoyloxy,2,6-dimethyl-4-tert-butylbenzoyloxy and 3,5-di-tert-butylbenzoyloxy.

Alkanoyl of up 25 carbon atoms is a branched or unbranched radical, forexample formyl, acetyl, propionyl, butanoyl, pentanoyl, hexanoyl,heptanoyl, octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl,tridecanoyl, tetradecanoyl, pentadecanoyl, hexadecanoyl, heptadecanoyl,octadecanoyl, eicosanoyl or docosanoyl. A preferred meaning of R₁ is C₁-C₁₈ alkanoyl. A particularly preferred meaning of R₁ is C₅ -C₁₀alkanoyl branched in the α position. A specifically preferred meaning ofR₁ is pivaloyl and 2,2-dimethyloctanoyl.

Alkenoyl of 3 to 25 carbon atoms is a branched or unbranched radical,for example propenoyl, 2-butenoyl, 3-butenoyl, isobutenoyl,n-2,4-pentadienoyl, 3-methyl-2-butenoyl, n-2-octenoyl, n-2-dodecenoyl,iso-dodecenoyl, oleoyl, n-2-octadecenoyl or n-4-octadecenoyl.

Examples of C₃ -C₂₅ alkanoyl which is interrupted by oxygen, sulfur or>N--R₁₆ are CH₃ --O--CH₂ CO--, CH₃ --S--CH₂ CO--, CH₃ --NH--CH₂ CO--,CH₃ --N(CH₃)--CH₂ CO--, CH₃ --O--CH₂ CH₂ --O--CH₂ CO--, CH₃ --(O--CH₂CH₂ --)₂ O--CH₂ CO--, CH₃ --(O--CH₂ CH₂ --)₃ O--CH₂ CO-- and CH₃--(O--CH₂ CH₂ --)₄ O--CH₂ CO--. Methoxyacetyl is preferred.

Examples of C₆ -C₉ cycloalkylcarbonyl are cyclopentylcarbonyl,cyclohexylcarbonyl, cycloheptylcarbonyl and cyclooctylcarbonyl.Cyclohexylcarbonyl is preferred.

Examples of C₁ -C₁₂ alkyl-substituted benzoyl are o-, m- orp-methylbenzoyl, 2,3-dimethylbenzoyl, 2,4-dimethylbenzoyl,2,5-dimethylbenzoyl, 2,6-dimethylbenzoyl, 3,4-dimethylbenzoyl,3,5-dimethylbenzoyl, 2-methyl-6-ethylbenzoyl, 4-tert-butylbenzoyl,2-ethylbenzoyl, 2,4,6-trimethylbenzoyl, 2,6-dimethyl-4-tert-butylbenzoyland 3,5-ditert-butylbenzoyl.

Alkylene of up to 18 carbon atoms is a branched or unbranched radical,for example methylene, ethylene, propylene, trimethylene,tetramethylene, pentamethylene, hexamethylene, heptamethylene,octamethylene, decamethylene, dodecamethylene or octadecamethylene. C₁-C₈ Alkylene is preferred.

Examples of C₂ -C₁₈ alkylene which is interrupted by oxygen, sulfur or>N--R₁₆ are --CH₂ --O--CH₂ --, --CH₂ --S--CH₂ --, --CH₂ --NH--CH₂ --,--CH₂ --N(CH₃)--CH₂ --, --CH₂ --O--CH₂ CH₂ --O--CH₂ --, --CH₂ --(O--CH₂CH₂ --)₂ O--CH₂ --, --CH₂ --(O--CH₂ CH₂ --)₃ O--CH₂ -- and --CH₂--(O--CH₂ CH₂ --)₄ O--CH₂ --.

Examples of alkenylene of 2 to 18 carbon atoms are vinylene,methylvinylene, octenylethylene and dodecenylethylene. C₂ -C₈ Alkenyleneis preferred.

Examples of alkylidene of 2 to 20 carbon atoms are ethylidene,propylidene, butylidene, pentylidene, 4-methylpentylidene, heptylidene,nonylidene, tridecylidene, nonadecylidene, 1-methylethylidene,1-ethylpropylidene and 1-ethylpentylidene. C₂ -C₈ Alkylidene ispreferred.

Examples of phenylalkylidene of 7 to 20 carbon atoms are benzylidene,2-phenylethylidene and 1-phenyl-2-hexylidene. C₇ -C₉ phenylalkylidene ispreferred.

C₅ -C₈ Cycloalkylene is a saturated hydrocarbon group having two freevalences and at least one ring unit and is, for example, cyclopentylene,cyclohexylene, cycloheptylene or cyclooctylene. Cylcohexylene ispreferred.

Examples of C₇ -C₈ bicycloalkylene are bicycloheptylene andbicyclooctylene.

Examples of phenylene are 1,2-, 1,3- and 1,4-phenylene. 1,2- and1,4-phenylene are preferred.

A mono-, di- or trivalent metal cation is preferably an alkali metalcation, alkaline earth metal cation or aluminium cation, for exampleNa⁺, K⁺, Mg⁺⁺, Ca⁺⁺ or Al⁺⁺⁺.

Of interest are compositions containing compounds of the formula (1) inwhich R₂, R₃, R₄ and R₅, independently of one another, are hydrogen, C₁-C₁₈ alkyl, benzyl, phenyl, C₅ -C₈ -cycloalkyl, C₁ -C₈ alkoxy, hydroxyl,C₁ -C₁₈ alkanoyloxy, C₃ -C₁₈ alkenoyloxy or benzoyloxy, R₄ isadditionally --(CH₂)_(n) --COR₁₁, and, in the case where m is 1, R₁ ishydrogen, C₁ -C₁₈ alkanoyl, C₃ -C₁₈ alkenoyl, C₃ -C₁₈ alkanoyl which isinterrupted by oxygen, sulfur or >N--R₁₆ ; C₆ -C₉ cycloalkylcarbonyl,benzoyl or C₁ -C₈ alkyl-substituted benzoyl, R₁₆ is as defined aboveand, in the case where m is 2, R₁ is ##STR11## in which R₁₇ is a directbond, C₁ -C₁₂ alkylene, C₂ -C₁₂ alkylene which is interrupted by oxygen,sulfur or >N--R₁₆ ; C₂ -C₁₂ alkenylene, C₂ -C₁₂ alkylidene, C₇ -C₁₂phenylalkylidene, C₅ -C₈ cycloalkylene or phenylene and R₁₆ is asdefined above.

Preference is given to compositions in which in formula (1) at least twoof the radicals R₂, R₃, R₄ and R₅ are hydrogen.

Preference is also given to compositions in which in formula (1) R₃ andR₅ are hydrogen.

Preference is likewise given to compositions in which in formula (1) R₃,R₅, R₇ and R₁₀, independently of one another, are hydrogen or C₁ -C₄alkyl, R₂ is hydrogen or C₁ -C₁₈ alkyl, R₄ is hydrogen, C₁ -C₁₂ alkyl,C₁ -C₈ alkoxy, hydroxyl or --(CH₂)_(n) --COR₁₁, in which n is 0, 1 or 2,R₁₁ is hydroxyl or C₁ -C₁₂ alkoxy, and, in the case where m is 1, R₁ ishydrogen, C₁ -C₁₈ alkanoyl, C₃ -C₁₈ alkanoyl which is interrupted byoxygen; or C₃ -C₁₈ alkenoyl, and, in the case where m is 2, R₁ is##STR12## in which R₁₇ is C₁ -C₈ alkylene, C₂ -C₈ alkenylene, C₂ -C₈alkylidene, C₇ -C₉ phenylalkylidene, cyclohexylene or phenylene.

Preference is also given to compositions in which in formula (1) R₂ ishydrogen or C₁ -C₁₄ alkyl, R₃ and R₅ are hydrogen, R₄ is hydrogen,hydroxyl, C₁ -C₄ alkyl, C₁ -C₄ alkoxy or --(CH₂)_(n) --COR₁₁, in which nis 2 and R₁₁ is hydroxyl, R₇, R₈, R₉ and R₁₀, independently of oneanother, are hydrogen, C₁ -C₄ alkyl or C₁ -C₄ alkoxy, with the provisothat at least one of the radicals R₇, R₈, R₉ or R₁₀ is hydrogen, m is 1and R₁ is hydrogen, C₁ -C₁₈ alkanoyl, C₃ -C₈ alkanoyl which isinterrupted by oxygen; or is C₃ -C₄ alkenoyl and R₆ is hydrogen or aradical of the formula (3) ##STR13## in which R₁, R₂, R₃, R₄, R₅, R₇,R₈, R₉ and R₁₀ are as defined above.

Particular preference is given to compositions in which in formula (1)R₂ is hydrogen or C₁ -C₁₄ alkyl, R₃, R₅, R₆, R₇ and R₁₀ are hydrogen, R₄is hydrogen or C₁ -C₄ alkyl, R₈ and R₉, independently of one another,are hydrogen, C₁ -C₄ alkyl or C₁ -C₄ alkoxy, m is 1 and R₁ is C₁ -C₁₀alkanoyl or C₃ -C₄ alkenoyl.

The compounds according to the invention of the formula (1) are suitablefor the stabilisation of organic materials against oxidative, thermaland/or light-induced degradation.

Examples of such materials are:

1. Polymers of monoolefins and diolefins, for example polypropylene,polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene orpolybutadiene, as well as polymers of cycloolefins, for instance ofcyclopentene or norbornene, polyethylene (which optionally can becrosslinked), for example high density polyethylene (HDPE), low densitypolyethylene (LDPE), linear low density polyethylene (LLDPE), branchedlow density polyethylene (BLDPE).

Polyolefins, i.e. the polymers of monoolefins exemplified in thepreceding paragraph, preferably polyethylene and polypropylene, can beprepared by different, and especially by the following, methods:

a) radical polymerisation (normally under high pressure and at elevatedtemperature).

b) catalytic polymerisation using a catalyst that normally contains oneor more than one metal of groups IVb, Vb, VIb or VIII of the PeriodicTable. These metals usually have one or more than one ligand, typicallyoxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenylsand/or aryls that may be either π- or σ-coordinated. These metalcomplexes may be in the free form or fixed on substrates, typically onactivated magnesium chloride, titanium(III) chloride, alumina or siliconoxide. These catalysts may be soluble or insoluble in the polymerisationmedium. The catalysts can be used by themselves in the polymerisation orfurther activators may be used, typically metal alkyls, metal hydrides,metal alkyl halides, metal alkyl oxides or metal alkyloxanes, saidmetals beeing elements of groups Ia, IIa and/or IIIa of the PeriodicTable. The activators may be modified conveniently with further ester,ether, amine or silyl ether groups. These catalyst stystems are usuallytermed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont),metallocene or single site catalysts (SSC).

2. Mixtures of the polymers mentioned under 1), for example mixtures ofpolypropylene with polyisobutylene, polypropylene with polyethylene (forexample PP/HDPE, PP/LDPE) and mixtures of different types ofpolyethylene (for example LDPE/HDPE).

3. Copolymers of monoolefins and diolefins with each other or with othervinyl monomers, for example ethylene/propylene copolymers, linear lowdensity polyethylene (LLDPE) and mixtures thereof with low densitypolyethylene (LDPE), propylene/but1ene copolymers, propylene/isobutylenecopolymers, ethylene/but-1-ene copolymers, ethylene/hexene copolymers,ethylene/methylpentene copolymers, ethylene/heptene copolymers,ethylene/octene copolymers, propylene/butadiene copolymers,isobutylene/isoprene copolymers, ethylene/alkyl acrylate copolymers,ethylene/alkyl methacrylate copolymers, ethylene/vinyl acetatecopolymers and their copolymers with carbon monoxide or ethylene/acrylicacid copolymers and their salts (ionomers) as well as terpolymers ofethylene with propylene and a diene such as hexadiene, dicyclopentadieneor ethylidene-norbornene; and mixtures of such copolymers with oneanother and with polymers mentioned in 1) above, for examplepolypropylene/ethylene-propylene copolymers, LDPE/ethylene-vinyl acetatecopolymers (EVA), LDPE/ethylene-acrylic acid copolymers (EAA),LLDPE/EVA, LLDPE/EAA and alternating or random polyalkylene/carbonmonoxide copolymers and mixtures thereof with other polymers, forexample polyamides.

4. Hydrocarbon resins (for example C₅ -C₉) including hydrogenatedmodifications thereof (e.g. tackifiers) and mixtures of polyalkylenesand starch.

5. Polystyrene, poly(p-methylstyrene), poly(α-methylstyrene).

6. Copolymers of styrene or α-methylstyrene with dienes or acrylicderivatives, for example styrene/butadiene, styrene/acrylonitrile,styrene/alkyl methacrylate, styrene/butadiene/alkyl acrylate,styrene/butadiene/alkyl methacrylate, styrene/maleic anhydride,styrene/acrylonitrile/methyl acrylate; mixtures of high impact strengthof styrene copolymers and another polymer, for example a polyacrylate, adiene polymer or an ethylene/propylene/diene terpolymer; and blockcopolymers of styrene such as styrene/butadiene/styrene,styrene/isoprene/styrene, styrene/ethylene/butylene/styrene orstyrene/ethylene/propylene/styrene.

7. Graft copolymers of styrene or α-methylstyrene, for example styreneon polybutadiene, styrene on polybutadiene-styrene orpolybutadiene-acrylonitrile copolymers; styrene and acrylonitrile (ormethacrylonitrile) on polybutadiene; styrene, acrylonitrile and methylmethacrylate on polybutadiene; styrene and maleic anhydride onpolybutadiene; styrene, acrylonitrile and maleic anhydride or maleimideon polybutadiene; styrene and maleimide on polybutadiene; styrene andalkyl acrylates or methacrylates on polybutadiene; styrene andacrylonitrile on ethylene/propylene/diene terpolymers; styrene andacrylonitrile on polyalkyl acrylates or polyalkyl methacrylates, styreneand acrylonitrile on acrylate/butadiene copolymers, as well as mixturesthereof with the copolymers listed under 6), for example the copolymermixtures known as ABS, MBS, ASA or AES polymers.

8. Halogen-containing polymers such as polychloroprene, chlorinatedrubbers, chlorinated or sulfochlorinated polyethylene, copolymers ofethylene and chlorinated ethylene, epichlorohydrin homo- and copolymers,especially polymers of halogen-containing vinyl compounds, for examplepolyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride,polyvinylidene fluoride, as well as copolymers thereof such as vinylchloride/vinylidene chloride, vinyl chloride/vinyl acetate or vinylidenechloride/vinyl acetate copolymers.

9. Polymers derived from α,β-unsaturated acids and derivatives thereofsuch as polyacrylates and polymethacrylates; polymethyl methacrylates,polyacrylamides and polyacrylonitriles, impact-modified with butylacrylate.

10. Copolymers of the monomers mentioned under 9) with each other orwith other unsaturated monomers, for example acrylonitrile/butadienecopolymers, acrylonitrile/alkyl acrylate copolymers,acrylonitrile/alkoxyalkyl acrylate or acrylonitrile/vinyl halidecopolymers or acrylonitrile/alkyl methacrylate/butadiene terpolymers.

11. Polymers derived from unsaturated alcohols and amines or the acylderivatives or acetals thereof, for example polyvinyl alcohol, polyvinylacetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate,polyvinyl butyral, polyallyl phthalate or polyallyl melamine; as well astheir copolymers with olefins mentioned in 1) above.

12. Homopolymers and copolymers of cyclic ethers such as polyalkyleneglycols, polyethylene oxide, polypropylene oxide or copolymers thereofwith bisglycidyl ethers.

13. Polyacetals such as polyoxymethylene and those polyoxymethyleneswhich contain ethylene oxide as a comonomer; polyacetals modified withthermoplastic polyurethanes, acrylates or MBS.

14. Polyphenylene oxides and sulfides, and mixtures of polyphenyleneoxides with styrene polymers or polyamides.

15. Polyurethanes derived from hydroxyl-terminated polyethers,polyesters or polybutadienes on the one hand and aliphatic or aromaticpolyisocyanates on the other, as well as precursors thereof.

16. Polyamides and copolyamides derived from diamines and dicarboxylicacids and/or from aminocarboxylic acids or the corresponding lactams,for example polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12,4/6, 12/12, polyamide 11, polyamide 12, aromatic polyamides startingfrom m-xylene diamine and adipic acid; polyamides prepared fromhexamethylenediamine and isophthalic off and terephthalic acid and withor without an elastomer as modifier, for examplepoly-2,4,4,-trimethylhexamethylene terephthalamide or poly-m-phenyleneisophthalamide; and also block copolymers of the aforementionedpolyamides with polyolefins, olefin copolymers, ionomers or chemicallybonded or grafted elastomers; or with polyethers, e.g. with polyethyleneglycol, polypropylene glycol or polytetramethylene glycol; as well aspolyamides or copolyamides modified with EPDM or ABS; and polyamidescondensed during processing (RIM polyamide systems).

17. Polyureas, polyimides, polyamide-imides and polybenzimidazoles.

18. Polyesters derived from dicarboxylic acids and diols and/or fromhydroxycarboxylic acids or the corresponding lactones, for examplepolyethylene terephthalate, polybutylene terephthalate,poly-1,4-dimethylolcyclohexane terephthalate and polyhydroxybenzoates,as well as block copolyether esters derived from hydroxyl-terminatedpolyethers; and also polyesters modified with polycarbonates or MBS.

19. Polycarbonates and polyester carbonates.

20. Polysulfoncs, polyether sulfones and polyether ketones.

21. Crosslinked polymers derived from aldehydes on the one hand andphenols, ureas and melamines on the other hand, such asphenol/formaldehyde resins, urea/formaldehyde resins andmelamine/formaldehyde resins.

22. Drying and non-drying alkyd resins.

23. Unsaturated polyester resins derived from copolyesters of saturatedand unsaturated dicarboxylic acids with polyhydric alcohols and vinylcompounds as crosslinking agents, and also halogen-containingmodifications thereof of low flammability.

24. Crosslinkable acrylic resins derived from substituted acrylates, forexample epoxy acrylates, urethane acrylates or polyester acrylates.

25. Alkyd resins, polyester resins and acrylate resins crosslinked withmelamine resins, urea resins, polyisocyanates or epoxy resins.

26. Crosslinked epoxy resins derived from polyepoxides, for example frombisglycidyl ethers or from cycloaliphatic diepoxides.

27. Natural polymers such as cellulose, rubber, gelatin and chemicallymodified homologous derivatives thereof, for example cellulose acetates,cellulose propionates and cellulose butyrates, or the cellulose etherssuch as methyl cellulose; as well as rosins and their derivatives.

28. Blends of the aforementioned polymers (polyblends), for examplePP/EPDM, Polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS,PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates, POM/thermoplastic PUR,PC/thermoplastic PUR, POM/acrylate, POM/MBS, PPO/HIPS, PPO/PA 6.6 andcopolymers, PA/HDPE, PA/PP, PA/PPO.

29. Naturally occurring and synthetic organic materials which are puremonomeric compounds or mixtures of such compounds, for example mineraloils, animal and vegetable fats, oil and waxes, or oils, fats and waxesbased on synthetic esters (e.g. phthalates, adipates, phosphates ortrimellitates) and also mixtures of synthetic esters with mineral oilsin any weight ratios, typically those used as spinning compositions, aswell as aqueous emulsions of such materials.

30. Aqueous emulsions or natural or synthetic rubber, e.g. natural latexor latices of carboxylated styrene/butadiene copolymers.

Preferred organic materials are polymers, for example syntheticpolymers, in particular thermoplastic polymers. Polyolefins andpolyurethanes are particularly preferred. Examples of preferredpolyolefins are polypropylene or polyethylene.

The compositions according to the invention also serve for thepreparation of polyurethanes, in particular for the preparation offlexible polyurethane foams. The compositions according to the inventionand the products prepared therefrom are effectively protected againstdegradation. In particular, scorching during foam manufacture isavoided.

The polyurethanes are obtained, for example, by reaction of polyethers,polyesters and polybutadienes containing terminal hydroxyl groups withaliphatic or aromatic polyisocyanates.

Polyethers containing terminal hydroxyl groups are known and areprepared, for example, by polymerisation of epoxides, such as ethyleneoxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxideor epichlorohydrin with themselves, for example in the presence of BF₃,or by addition reaction of these epoxides, if desired in a mixture or insuccession, with starting components containing reactive hydrogen atoms,such as water, alcohols, ammonia or amines, for example ethylene glycol,1,3- and 1,2-propylene glycol, trimethylolpropane,4,4'-dihydroxydiphenylpropane, aniline, ethanolamine or ethylenediamine.According to the invention, sucrose polyethers are also suitable. Inmany cases, those polyethers are preferred which predominantly (up to90% by weight, relative to all OH groups present in the polyether)contain primary OH groups. Polyethers modified by vinyl polymers, suchas are formed, for example, by polymerisation of styrene andacrylonitrile in the presence of polyethers, are also suitable, as arepolybutadienes containing OH groups.

These compounds generally have molecular weights of 400-10,000. They arepolyhydroxy compounds, in particular compounds containing two to eighthydroxyl groups, specifically those of molecular weight 800 to 10,000,preferably 1000 to 6000, for example polyethers containing at least two,usually 2 to 8, but preferably 2 to 4, hydroxyl groups, such as areknown per se for the preparation of homogeneous and of cellularpolyurethanes.

It is of course also possible to use mixtures of the abovementionedcompounds which contain at least two hydrogen atoms which are reactivewith isocyanates, in particular those having a molecular weight of400-10,000.

Suitable polyisocyanates are aliphatic, cycloaliphatic, araliphatic,aromatic and heterocyclic polyisocyanates, for example ethylenediisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylenediisocyanate, 1,12-diisocyanatododecane, 1,3-cyclobutane diisocyanate,1,3- and 1,4-cyclohexane diisocyanate and any desired mixtures of theseisomers, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane,2,4- and 2,6-hexahydrotoluylene diisocyanate and any desired mixtures ofthese isomers, 1,3- and/or 1,4-hexahydrophenylene diisocyanate, 2,4'-and/or 4,4'-diisocyanatoperhydrodiphenylmethane, 1,3- and 1,4-phenylenediisocyanate, 2,4- and 2,6-toluylene diisocyanate and any desiredmixtures of these isomers, 2,4'- and/or4,4'-diisocyanatodiphenylmethane, 1,5-naphthylene diisocyanate,4,4',4"-triisocyanatotriphenylmethane, polyphenylpolymethylenepolyisocyanates, such as are obtained by aniline/formaldehydecondensation, followed by phosgenation, m- andp-isocyanatophenylsulfonyl isocyanates, perchlorinated arylpolyisocyanates, polyisocyanates containing carbodiimide groups,polyisocyanates containing allophanate groups, polyisocyanatescontaining isocyanurate groups, polyisocyanates containing urethanegroups, polyisocyanates containing acylated urea groups, polyisocyanatescontaining biuret groups, polyisocyanates containing ester groups,reaction products of the abovementioned isocyanates with acetals, andpolyisocyanates containing polymeric fatty acid radicals.

It is also possible to use the isocyanato-containing distillationresidues formed in the industrial preparation of isocyanates, if desireddissolved in one or more of the abovementioned polyisocyanates.Furthermore, it is possible to use any desired mixtures of theabovementioned polyisocyanates.

Particular preference is usually given to the industrially readilyaccessible polyisocyanates, for example 2,4- and 2,6-toluylenediisocyanate and any desired mixtures of these isomers ("TDI"),polyphenyl polymethylene polyisocyanates such as are prepared byaniline/formaldehyde condensation, followed by phosgenation ("crudeMDI"), and polyisocyanates containing carbodiimide groups, urethanegroups, allophanate groups, isocyanurate groups, urea groups or biuretgroups ("modified polyisocyanates").

The activity of the compounds according to the invention against thermaland oxidative degradation, especially upon thermal stress, such asoccurs during processing of thermoplastics, may be mentioned inparticular. Accordingly, the compounds according to the invention arehighly suitable for use as processing stabilisers.

Preferably, the compounds of the formula (1) are added to the materialto be stabilised in amounts of 0.0005 to 5%, in particular 0.001 to 2%,for example 0.01 to 2%, relative to the weight of the organic materialto be stabilised.

The compositions according to the invention can contain, in addition tothe compounds of the formula (1), further costabilisers, for example theones listed below:

1. Antioxidants

1.1. Alkylated monophenols, for example2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol,2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol,2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol,2-(α-methylcyclohexyl)-4,6-dimethylphenol,2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol,2,6-di-tert-butyl-4-methoxymethylphenol, 2,6-di-nonyl-4-methylphenol,2,4-dimethyl-6-(1'-methylundec-1'-yl)phenol,2,4-dimethyl-6-(1'-methylheptadec-1'-yl)phenol,2,4-dimethyl-6-(1'-methyltridec-1'-yl)phenol and mixtures thereof.

1.2. Alkylthiomethylphenols, for example2,4-dioctylthiomethyl-6-tert-butylphenol,2,4-dioctylthiomethyl-6-methylphenol,2,4-dioctylthiomethyl-6-ethylphenol,2,6-di-dodecylthiomethyl-4-nonylphenol.

1.3. Hydroquinones and alkylated hydroquinones, for example2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone,2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol,2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole,3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenylstearate, bis-(3,5-di-tert-butyl-4-hydroxyphenyl) adipate.

1.4. Hydroxylated thiodiphenyl ethers, for example2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol),4,4'-thiobis(6-tert-butyl-3-methylphenol),4,4'-thiobis(6-tert-butyl-2-methylphenol),4,4'-thiobis-(3,6-di-sec-amylphenol),4,4'-bis-(2,6-dimethyl-4-hydroxyphenyl) disulfide.

1.5. Alkylidenebisphenols, for example2,2'-methylenebis(6-tert-butyl-4-methylphenol),2,2'-methylenebis(6-tert-butyl-4-ethylphenol),2,2'-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol],2,2'-methylenebis(4-methyl-6-cyclohexylphenol),2,2'-methylenebis(6-nonyl-4-methylphenol),2,2'-methylenebis(4,6-di-tert-butylphenol),2,2'-ethylidenebis(4,6-di-tert-butylphenol),2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol),2,2'-methylenebis[6-(α-methylbenzyl)-4-nonylphenol],2,2'-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol],4,4'-methylenebis(2,6-di-tert-butylphenol),4,4'-methylenebis(6-tert-butyl-2-methylphenol),1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butane,2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol,1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane,1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecylmercaptobutane,ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate],bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)dicyclopentadiene,bis[2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalate,1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)butane,2,2-bis-(3,5-di-tert-butyl-4-hydroxyphenyl)propane,2,2-bis-(5-tert-butyl-4-hydroxy2-methylphenyl)-4-n-dodecylmercaptobutane,1,1,5,5-tetra-(5-tert-butyl-4-hydroxy2-methylphenyl)pentane.

1.6. O--, N-- and S-benzyl compounds, for example3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether,octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate,tris-(3,5-di-tert-butyl-4-hydroxybenzyl)amine,bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate,bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide,isooctyl-3,5di-tert-butyl-4-hydroxybenzylmercaptoacetate.

1.7. Hydroxybenzylated malonates, for exampledioctadecyl-2,2-bis-(3,5-di-tert-butyl-2-hydroxybenzyl)-malonate,di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)-malonate,di-dodecylmercaptoethyl-2,2-bis-(3,5-di-tert-butyl-4-hydroxybenzyl)malonate,bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.

1.8. Aromatic hydroxybenzyl compounds, for example1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene,1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene,2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.

1.9. Triazine Compounds, for example2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine,2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine,2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine,2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine,1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate,1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate,2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine,1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexahydro-1,3,5-triazine,1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate.

1.10. Benzylphosphonates, for exampledimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate,diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate,dioctadecyl3,5-di-tert-butyl-4-hydroxybenzylphosphonate,dioctadecyl-5-tert-butyl-4-hydroxy3-methylbenzylphosphonate, the calciumsalt of the monoethyl ester of3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid.

1.11. Acylaminophenols, for example 4-hydroxylauranilide,4-hydroxystearanilide, octylN-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.

1.12. Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid withmono- or polyhydric alcohols, e.g. with methanol, ethanol, octadecanol,1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol,neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethyleneglycol, pentaerythritol, tris(hydroxyethyl) isocyanurate,N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol,trimethylhexanediol, trimethylolpropane,4-hydroxymethyl-1-phospha-2,6,7- trioxabicyclo[2.2.2]octane.

1.13. Esters of β-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acidwith mono- or polyhydric alcohols, e.g. with methanol, ethanol,octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol,1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethyleneglycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol,3-thiapentadecanol, trimethylhexanediol, trimethylolpropane,4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

1.14 Esters of β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid withmono- or polyhydric alcohols, e.g. with methanol, ethanol, octadecanol,1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol,neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethyleneglycol, pentaerythritol, tris(hydroxyethyl) isocyanurate,N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol,trimethylhexanediol, trimethylolpropane,4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

1.15 Esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid with mono-or polyhydric alcohols, e.g. with methanol, ethanol, octadecanol,1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol,neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethyleneglycol, pentaerythritol, tris(hydroxyethyl) isocyanurate,N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol,trimethylhexanediol, trimethylolpropane,4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2] octane.

1.16. Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid e.g.N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine,N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine,N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine.

2. UV Absorbers and Light Stabilisers

2.1. 2-(2'-Hydroxyphenyl)benzotriazoles, for example2-(2'-hydroxy-5'-methylphenyl)benzotriazole,2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole,2-(5'-tert-butyl-2'-hydroxyphenyl)benzotriazole2-(2'-hydroxy-5'-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole,2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)-5-chloro-benzotriazole,2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)-5-chloro-benzotriazole,2-(3'-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl)benzotriazole2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazole,2-(3',5'-di-tert-amyl-2'-hydroxyphenyl)benzotriazole,2-(3',5'-bis-(α,α-dimethylbenzyl)-2'-hydroxyphenyl)benzotriazole,mixture of2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)-5-chloro-benzotriazole,2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)-carbonylethyl]-2'-hydroxyphenyl)-5-chloro-benzotriazole,2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-5-chloro-benzotriazole,2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole,2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)benzotriazole,2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)benzotriazole,2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl)benzotriazole, and2-(3'-tert-butyl-2'-hydroxy-5'-(2-isooctyloxycarbonylethyl)phenylbenzotriazole,2,2'-methylene-bis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazole-2-ylphenol];the transesterification product of2-[3'-tert-butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazolewith polyethylene glycol 300; [R--CH₂ CH₂ --COO(CH₂)₃ ]₂ ], whereR=3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl.

2.2. 2-Hydroxybenzophenones, for example the 4-hydroxy, 4-methoxy,4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxyand 2'-hydroxy-4,4'-dimethoxy derivatives.

2.3. Esters of substituted and unsubstituted benzoic acids, as forexample 4-tertbutylphenyl salicylate, phenyl salicylate, octylphenylsalicylate, dibenzoyl resorcinol, bis(4-tert-butylbenzoyl) resorcinol,benzoyl resorcinol, 2,4-di-tertbutylphenyl3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl3,5-di-tert-butyl-4-hydroxybenzoate.

2.4. Acrylates, for example ethyl α-cyano-β,β-diphenylacrylate, isooctylα-cyano-β,β-diphenylacrylate, methyl α-carbomethoxycinnamate, methylα-cyano-β-methyl-p-methoxycinnamate, butylα-cyano-β-methyl-p-methoxy-cinnamate, methylα-carbomethoxy-p-methoxycinnamate andN-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline.

2.5. Nickel compounds, for example nickel complexes of2,2'-thio-bis-[4-(1,1,3,3-tetramethylbutyl)phenol], such as the 1:1 or1:2 complex, with or without additional ligands such as n-butylamine,triethanolamine or N-cyclohexyldiethanolamine, nickeldibutyldithiocarbamate, nickel salts of the monoalkyl esters, e.g. themethyl or ethyl ester, of 4-hydroxy-3,5-di-tert-butylbenzylphosphonicacid, nickel complexes of ketoximes, e.g. of 2-hydroxy-4-methylphenylundecylketoxime, nickel complexes of1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additionalligands.

2.6. Sterically hindered amines, for examplebis(2,2,6,6-tetramethyl-piperidyl)sebacate,bis(2,2,6,6-tetramethyl-piperidyl)succinate,bis(1,2,2,6,6-pentamethylpiperidyl)sebacate,bis(1,2,2,6,6-pentamethylpiperidyl)n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinicacid, the condensate ofN,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and4-tert-octylamino-2,6-dichloro-1,3,5-triazine,tris(2,2,6,6-tetramethyl-4-piperidyl) nitrilotriacetate,tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butane-tetracarboxylate,1,1'-(1,2-ethanediyl)bis(3,3,5,5-tetramethylpiperazinone),4-benzoyl-2,2,6,6-tetramethylpiperidine,4-stearyloxy-2,2,6,6-tetramethylpiperidine,bis(1,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate,3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazasprio[4.5]decan-2,4-dion,bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)sebis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)succinate, the condensate ofN,N'-bis-(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and4-morpholino-2,6-dichloro-1,3,5-triazine, the condensate of2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)-1,3,5-triazine and 1,2-bis(3-aminopropylamino)ethane, the condensateof2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazineand 1,2-bis-(3-aminopropylamino)ethane,8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione,3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidin-2,5-dione,3-dodecyl-1-(1,2,2,6,6-pentamethyl-4-piperidyl)pyrrolidine-2,5-dione.

2.7. Oxamides, for example 4,4'-dioctyloxyoxanilide,2,2'-dioctyloxy-5,5'-di-tert-butoxanilide,2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethoxanilide,N,N'-bis(3-dimethylaminopropyl)oxamide,2-ethoxy-5-tert-butyl-2'-ethoxanilide and its mixture with2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide and mixtures of ortho- andparamethoxy-disubstituted oxanilides and mixtures of o- andp-ethoxy-disubstituted oxanilides.

2.8. 2-(2-Hydroxyphenyl)-1,3,5-triazines, for example2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine,2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine,2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine,2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,2-[2-hydroxy-4-(2hydroxy-3-butyloxy-propoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine,2-[2-hydroxy-4-(2-hydroxy-3-octyloxy-propyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine.

3. Metal deactivators, for example N,N'-diphenyloxamide,N-salicylal-N'-salicyloyl hydrazine, N,N'-bis(salicyloyl) hydrazine,N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazine,3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyl dihydrazide,oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide,N,N'-diacetyladipoyl dihydrazide, N,N'-bis(salicyloyl)oxalyldihydrazide, N,N'-bis(salicyloyl)thiopropionyl dihydrazide.

4. Phosphites and phosphonites, for example triphenyl phosphite,diphenyl alkyl phosphites, phenyl dialkyl phosphites, tris(nonylphenyl)phosphite, trilauryl phosphite, trioctadecyl phosphite, distearylpentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl) phosphite,diisodecyl pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite,bis(2,6-di-tert-butyl-4-methylphenyl)-pentaeryt hritol diphosphite,diisodecyloxypentaerythritol diphosphite,bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite,bis(2,4,6-tris(tert-butylphenyl)pentaerythritol diphsophite, tristearylsorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)4,4'-biphenylene diphosphonite,6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioxaphosphocin,6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz[d,g]-1,3,2-dioxaphosphocin,bis(2,4-di-tert-butyl-6-methylphenyl)methylphosphite,bis(2,4-di-tert-butyl-6-methylphenyl)ethylphosphite.

5. Peroxide scavengers, for example esters of β-thiodipropionic acid,for example the lauryl, stearyl, myristyl or tridecyl esters,mercaptobenzimidazole or the zinc salt of 2-mercaptobenzimidazole, zincdibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritoltetrakis(β-dodecylmercapto)propionate.

6. Polyamide stabilisers, for example, copper salts in combination withiodides and/or phosphorus compounds and salts of divalent manganese.

7. Basic co-stabilisers, for example, melamine, polyvinylpyrrolidone,dicyandiamide, triallyl cyanurate, urea derivatives, hydrazinederivatives, amines, polyamides, polyurethanes, alkali metal salts andalkaline earth metal salts of higher fatty acids for example calciumstearate, zinc stearate, magnesium behenate, magnesium stearate, sodiumricinoleate and potassium palmitate, antimony pyrocatecholate or tinpyrocatecholate.

8. Nucleating agents, for example, 4-tert-butylbenzoic acid, adipicacid, diphenylacetic acid.

9. Fillers and reinforcing agents, for example, calcium carbonate,silicates, glass fibres, asbestos, talc, kaolin, mica, barium sulfate,metal oxides and hydroxydes, carbon black, graphite.

10. Other additives, for example, plasticisers, lubricants, emulsifiers,pigments, optical brighteners, flameproofing agents, antistatic agentsand blowing agents.

The costabilisers are added, for example, in concentrations of 0.01 to10%, relative to the total weight of the material to be stabilised.

Incorporation of the compounds of the formula (1) and, if desired,further additives into the polymeric, organic material is carried out byknown methods, for example before or during moulding or else by applyingthe dissolved or dispersed compounds to the polymeric, organic material,if appropriate with subsequent slow evaporation of the solvent. Thecompounds of the formula (1) can also be added to the materials to bestabilised in the form of a masterbatch containing them, for example, ina concentration of 2.5 to 25% by weight.

The compounds of the formula (1) can also be added before or duringpolymerisation or before crosslinking.

The compounds of the formula (1) can be incorporated into the materialto be stabilised in pure form or encapsulated in waxes, oils orpolymers.

The compounds of the formula (1) can also be sprayed onto the polymer tobe stabilised. They are capable of diluting other additives (for examplethe abovementioned customary additives) or melts thereof, as a result ofwhich they can also be sprayed onto the polymer to be stabilisedtogether with these additives. Addition by spraying during deactivationof the polymerisation catalysts, it being possible, for example, for thevapour used for deactivation to be used for spraying, is particularlyadvantageous.

In the case of bead-polymerised polyolefins, it may be advantageous, forexample, to apply the compounds of the formula (1), if appropriatetogether with other additives, by spraying.

The materials thus stabilised can be used in various forms, for exampleas films, fibres, ribbons, moulded materials, profiles or as binders forpaints, adhesives or cement.

In the preparation of polyurethanes, it is possible also to add waterand/or highly volatile organic substances as blowing agents. Examples ofsuitable organic blowing agents are acetone, ethyl acetate,halogen-substituted alkanes, such as methylene chloride, chloroform,ethylidene chloride, vinylidene chloride, monofluorotrichlormethane,chlorodifluoromethane, dichlorodifluoromethane, furthermore butane,hexane, heptane or diethyl ether. A blowing effect can also be achievedby addition of compounds which decompose at temperatures above roomtemperature with the elimination of gases, for example of nitrogen, forexample azo compounds such as azoisobutyronitrile.

The preparation of polyurethanes is advantageously carried out in thepresence of suitable catalysts. The compounds used as such catalysts arecatalysts known per se, for example tertiary amines, such astriethylamine, tributylamine, N-methylmorpholine, N-ethylmorpholine,N-cocomorpholine, N,N,N',N'-tetramethylethylenediamine,1,4-diazabicyclo[2.2.2]octane, N-methyl-N'-dimethylaminoethylpiperazine,N,N-dimethylbenzylamine, bis(N,N-diethylaminoethyl) adipate, N,N-diethylbenzylamine, pentamethyldiethylenetriamine,N,N-dimethylcyclohexylamine, N,N,N',N'-tetramethyl-1,3-butanediamine,N,N-dimethyl-β-phenylethylamine, 1,2-dimethylimidazole and2-methylimidazole, furthermore Mannich bases known per se and obtainedfrom secondary amines, such as diethylamine, and aldehydes, preferablyformaldehyde, or ketones, such as acetone, methyl ethyl ketone orcyclohexanone, and phenols, such as phenol, nonylphenol or bisphenol.

Examples of tertiary amines containing hydrogen atoms which are activetowards isocyanate groups as catalysts are triethanolamine,triisopropanolamine, N-methyldiethanolamine, N-ethyldiethanolamine,N,N-dimethylethanolamine, and reaction products thereof with alkyleneoxides, such as propylene oxide and/or ethylene oxide.

Further suitable catalysts are also silaamines containingcarbon-silicone bonds, for example 2,2,4-trimethyl-2-silamorpholine and1,3-diethylaminomethyltetramethyldisiloxane, furthermorenitrogen-containing bases, such as tetraalkylammonium hydroxides,furthermore alkali metal hydroxides, such as sodium hydroxide, alkalimetal phenolates, such as sodium phenolate or alkali metal alcoholates,such as sodium methoxide, or hexahydrotriazines, furthermore organicmetal compounds, in particular organic tin compounds, for exampletin(II) salts of carboxylic acids, such as tin(II) acetate, tin(II)octoate, tin(II) ethylhexoate and tin(II) laurate, and tin(IV)compounds, for example dibutyltin oxide, dibutyltin dichloride,dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate ordioctyltin diacetate. It is of course also possible to use all of theabovementioned catalysts as mixtures.

If desired, further additives known per se, for example surface-activeadditives, such as emulsifiers and foam stabilisers, may be present.

Examples of suitable emulsifiers are the sodium salts of castor oilsulfonates or salts of fatty acids with amines, such as diethylamineoleate or diethanolamine stearate. Alkali metal salts or ammonium saltsof sulfonic acids, for example of dodecylbenzenesulfonic acid ordinaphthylmethanedisulfonic acid, or of fatty acids, such as ricinolicacid, or of polymer fatty acids can also be used as surface-activeadditives.

Suitable foam stabilisers are in particular polyether siloxanes,specifically water-soluble representatives. In general, the structure ofthese compounds is such that an ethylene oxide/propylene oxide copolymeris linked to a polydimethylsiloxane radical.

Further additives which may be present in the compositions are reactionretarders, for example acidic substances, such as hydrochloric acid ororganic acid halides, furthermore cell regulators of the type known perse, such as paraffins or fatty alcohols, or dimethylpolysiloxanes andpigments or dyes and flame retardants of the type known per se, forexample tris(chloroethyl) phosphate, tricresyl phosphate or ammoniumphosphate and ammonium polyphosphate, furthermore stabilisers againstthe effects of ageing and weather, plasticisers and substances acting asfungistats and bacteriostats and fillers, such as barium sulfate,kieselguhr, carbon black or precipitated chalk.

Further examples of surface-active additives and foam stabilisers andcell regulators, reaction retarders, stabilisers, flame retardants,plasticisers, dyes and fillers and substances acting as fungistats andbacteriostats which may be present and details on how these additivesare used and on their mode of action are well known to one skilled inthe art.

The polyurethane materials can be prepared in any desired form, forexample in the form of fibres. However, it is preferred to preparefoams, a suitable selection of the components resulting either inelastic or rigid foam materials or in all products between theseextremes.

Polyurethane foams are preferably prepared from liquid startingcomponents, the starting materials to be reacted with one another beingeither mixed with one another in a one-step process or, alternatively, apreadduct containing NCO groups being first prepared from a polyol andan excess of polyisocyanate, which is then foamed, for example byreaction with water.

The reactants are made to react by the known one-step process, theprepolymer process or the semi prepolymer process, in which use is oftenmade of mechanical equipment which is well known to the person skilledin the art.

In foam production, foaming is often carried out in moulds, the reactionmixture being introduced into a mould. Examples of suitable mouldmaterials are metals, for example aluminium, or plastics, for exampleepoxy resin. In the mould, the foamable reaction mixture expands andforms the moulded article. Foam moulding can be carded out in such amanner that the moulded part exhibits cell structure at its surface, butit can also be carried out in such a manner that the moulded panexhibits a compact skin and a cellular core. The procedure in this foamproduction can be such that the amount of foamable reaction mixtureintroduced into the mould is such that the resulting foam just aboutcompletely fills the mould. However, the procedure can also be such thatmore foamable reaction mixture is introduced into the mould than isnecessary for completely filling the interior of the mould with foam.Accordingly, in the last-mentioned case, foam production takes placewith "overcharging".

In foam moulding, the additional use of "external release agents" knownper se, such as silicone oils, is very common. However, it is alsopossible to use so-called "internal release agents", if appropriate inthe mixture with external release agents.

Cold-curing foams can also be produced. However, it is of course alsopossible to produce foams by block foaming or by the twin-belt methodknown per se.

It is also possible to produce flexible, semiflexible or rigidpolyurethane foams. They are used as known per se for such products, forexample as mattresses and upholstery in the furniture and automobileindustries, furthermore for the production of dashboards such as areused in the automobile industry and finally as insulating materials andmaterials for heat insulation and low-temperature insulation, forexample in the building sector or in the household refrigerator industryor in the textile industry, for example as shoulder pads.

The present invention also relates to a process for the stabilisation ofan organic material against oxidative, thermal or light-induceddegradation, which comprises incorporating therein or applying theretoat least one compound of the formula (1).

As already pointed out, the compounds according to the invention arealso particularly advantageously used as stabilisers in polyolefins, inparticular as thermal stabilisers. Excellent stabilisation is obtained,for example, by using them in combination with organic phosphites orphosphonites. In this combination, the advantage of the compoundsaccording to the invention is that they are already active in extremelysmall amounts. They are used, for example, in amounts of 0.0001 to0.015, in particular 0.0001 to 0.008, % by weight, relative to thepolyolefin. The organic phosphite or phosphonite is advantageously usedin an amount of 0.01 to 2, in particular 0.01 to 1, % by weight, alsorelative to the polyolefin. The organic phosphites or phosphonites usedare preferably those described in DE-A-4 202 276. See, in particular,the patent claims, the examples and pages 5, last paragraph, to page 11of this publication. For particularly advantageous phosphites andphosphonites, see also item 4 of the above list of costabilisers.

The invention also relates to novel compounds of the formula (1)##STR14## in which R₂, R₃, R₄ and R₅, independently of one another, arehydrogen, C₁ -C₂₅ alkyl, C₇ -C₉ phenylalkyl, unsubstituted or C₁ -C₄alkyl-substituted phenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅-C₈ cycloalkyl; C₁ -C₁₈ alkoxy, hydroxyl, C₁ -C₂₅ alkanoyloxy, C₃ -C₂₅-alkenoyloxy, C₃ -C₂₅ alkanoyloxy which is interrupted by oxygen, sulfuror >N--R₁₆ ; C₆ -C₉ -cycloalkylcarbonyloxy, benzoyloxy or C₁ -C₁₂alkyl-substituted benzoyloxy, where R₁₆ is hydrogen or C₁ -C₈ alkyl, or,furthermore, the radicals R₂ and R₃ or the radicals R₄ and R₅ togetherwith the carbon atoms to which they are bound form a phenyl ring, R₄ isadditionally --(CH₂)_(n) --COR₁₁, in which n is 0, 1 or 2, R₁₁ ishydroxyl, ##EQU3## C₁ -C₁₈ alkoxy or ##STR15## R₁₄ and R₁₅,independently of one another, are hydrogen or C₁ -C₁₈ alkyl, M is anr-valent metal cation and r is 1, 2 or 3, R₇, R₈, R₉ and R₁₀,independently of one another, are hydrogen, C₁ -C₄ alkyl or C₁ -C₄alkoxy, with the proviso that at least one of the radicals R₇, R₈, R₉and R₁₀ is hydrogen and, in the case where R₃, R₅, R₆, R₇ and R₁₀ arehydrogen, R₄ is additionally a radical of the formula (2) ##STR16## inwhich R₂, R₈ and R₉ are as defined above and R₁ is as defined below form=1, and R₁₂ and R₁₃, independently of one another, are hydrogen, C₁-C₁₂ alkyl or phenyl, m is 1 or 2, and,

in the case where m is 1,

R₁ is hydrogen, C₁ -C₂₅ alkanoyl, C₃ -C₂₅ alkenoyl, C₃ -C₂₅ alkanoylwhich is interrupted by oxygen, sulfur or >N--R₁₆ ; C₆ -C₉cycloalkylcarbonyl, benzoyl or C₁ -C₁₂ alkyl-substituted benzoyl, R₁₆ isas defined above and R₆ is hydrogen or a radical of the formula (3)##STR17## in which R₁, R₂, R₃, R₄, R₅, R₇, R₈, R₉ and R₁₀ are as definedabove, and,

in the case where m is 2,

R₁ is ##STR18## in which R₁₇ is a direct bond, C₁ -C₁₈ alkylene, C₂ -C₁₈alkylene which is interrupted by oxygen, sulfur or >N--R₁₆ ; C₂ -C₁₈alkenylene, C₂ -C₂₀ alkylidene, C₇ -C₂₀ phenylalkylidene, C₅ -C₈cycloalkylene, C₇ -C₈ bicycloalkylene or phenylene, R₁₆ is as definedabove and R₆ is hydrogen, with the exclusion of the compounds of theformula (4) to (8) ##STR19## in which X is hydrogen or acetyl.

Preferred groups of novel compounds of the formula (1) conform to thepreferences given above for the compositions according to the invention.

Preference is also given to compounds of the formula (1) in which R₃ andR₅ are hydrogen and at least one of the radicals R₂ and R₄ is nothydrogen.

Preference is also given to compounds of the formula (1) in which, inthe case where m is 1, R₁ is C₅ -C₂₅ alkanoyl, C₃ -C₂₅ alkanoyl which isinterrupted by oxygen, sulfur or >N--R₁₆ ; C₅ -C₈ cycloalkylcarbonyl,benzoyl or C₁ -C₁₂ alkyl-substituted benzoyl and R₁₆ is as definedabove.

Particular preference is given to compounds of the formula (1) in whichR₂ is hydrogen or C₁ -C₁₄ alkyl, R₃ and R₅ are hydrogen, R₄ is hydrogen,hydroxyl, C₁ -C₄ alkyl, C₁ -C₄ alkoxy or --(CH₂)_(n) --COR₁₁, in which nis 2 and R₁₁ is hydroxyl, R₇, R₈, R₉ and R₁₀, independently of oneanother, are hydrogen, C₁ -C₄ alkyl or C₁ -C₄ alkoxy, with the provisothat at least one of the radicals R₇, R₈, R₉ or R₁₀ is hydrogen, m is 1and R₁ is hydrogen, C₁ -C₁₈ alkanoyl, C₃ -C₈ alkanoyl which isinterrupted by oxygen; or is C₃ -C₄ alkenoyl and R₆ is hydrogen or aradical of the formula (3) ##STR20## in which R₁, R₂, R₃, R₄, R₅, R₇,R₈, R₉ and R₁₀ are as defined above.

Very particular preference is given to compounds of the formula (1) inwhich R₂ is hydrogen or C₁ -C₁₄ alkyl, R₃, R₅, R₆, R₇ and R₁₀ arehydrogen, R₄ is hydrogen or C₁ -C₄ alkyl, R₈ and R₉, independently ofone another, are hydrogen, C₁ -C₄ alkyl or C₁ -C₄ alkoxy, m is 1 and R₁is C₁ -C₁₀ alkanoyl or C₃ -C₄ alkenoyl.

The compounds according to the invention of the formula (1) can beprepared in a manner known per se.

For example, this being the preferred procedure, a phenol of the formula(9) ##STR21## in which R₂, R₃, R₄ and R₅ are as defined above, isreacted with a 4-hydroxymandelic acid substituted on the phenyl ring andhaving the formula (10), in which R₇, R₈, R₉ and R₁₀ are as defined, atelevated temperature, in particular at temperatures of 130° to 200° C.in the melt or in a solvent, if appropriate under a slight vacuum. Thereaction is preferably carried out in a solvent, for example acetic acidor formic acid, in a temperature range of from 50° to 130° C. Thereaction can be catalysed by addition of an acid, such as hydrochloricacid, sulfuric acid or methanesulfonic acid. The reaction can be carriedout, for example, in a manner such as described in the references givenin the introduction of the description.

The 4-hydroxymandelic acids substituted on the phenyl ring are known inthe literature or can be prepared analogously for example in accordancewith W. Bradley et al., J. Chem. Soc. 1956, 1622; EP-A-146269 or DE 2944 295.

The phenols of the formula (9) are also known or can be obtained bymethods known per se. ##STR22##

Bisphenol compounds of the formula (13) can be prepared in accordancewith Houben-Weyl, Methoden der organischen Chemic (Methods of OrganicChemistry), volume 6/1c, 1030.

The phenols of the formula (1) obtained by this reaction, in which R₁ ishydrogen, can be esterified by generally known esterification methods,for example in accordance with Organikum 1986, page 402-408, for exampleby acylation with an acid chloride or acid anhydride of the formula R₁ ¹Cl or R₁ ¹ --O--R₁ ¹ in which R₁ ¹ is R₁ except hydrogen. ##STR23##

Dimerisation of the compounds of the formula (11) in order to preparecompounds of the formula (1) in which R₆ is a group of the formula (3)[compounds of the formula (12)] is carried out by oxidation with, forexample, iodine under basic conditions in an organic solvent at roomtemperature. A suitable base in particular sodium ethoxide, and suitablesolvents are ethanol and diethyl ether.

The examples which follow illustrate the invention in more detail. Partsor percentages given therein are by weight.

EXAMPLE 1 Preparation of5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one (Compound (101),Table 1)

A mixture of 103.2 g (0.50 mol) of 2,4-di-tert-butylphenol and 102.4 g(0.55 mol) of 4-hydroxymandelic acid monohydrate in 100 ml of aceticacid is refluxed for 24 hours under a nitrogen atmosphere. The reactionmixture is then diluted with 140 ml of 50% aqueous acetic acid, cooled,and the precipitate formed is filtered off. The residue is washed withanother 200 ml of 50% aqueous acetic acid and then dried, giving 95.9 g(57%) of 5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one, meltingpoint 187°-190° C. (compound (101), Table 1).

EXAMPLE 2 Preparation of3-(3,5-dimethyl-4-hydroxyphenyl)-5,7-di-tert-butylbenzofuran-2-one(Compound (107), Table 1)

1.5 ml (23 mmol) of methanesulfonic acid are added to a mixture of 154.8g (0.75 mol) of 2,4-di-tert-butylphenol and 98.1 g (0.50 mol) of3,5-dimethyl-4-hydroxymandelic acid in 500 ml of acetic acid which isstirred at 95° C. under nitrogen. After about 4 minutes, crystallisationof the product in the form of fine, white crystals begins. The reactionmixture is refluxed for another hour, then cooled to about 15° C., andthe precipitated product is filtered off. The residue is washed with 250ml of acetic acid and with 1500 ml of water. Drying gives 161.5 g (88%)of 3-(3,5-dimethyl-4-hydroxyphenyl)-5,7-di-tert-butylbenzofuran-2-one,melting point 225°-228° C. (compound (107), Table 1).

The compounds (102), (103), (104), (105), (106), (108), (116), (126),(128), (130), (131), (132) and (134) are prepared from the correspondingphenols and mandelic acids analogously to Example 2.

Procedure for the preparation of substituted 4-hydroxymandelic acids:

0.30 mol of starting phenol are dissolved in 150 ml of 2N sodiumhydroxide solution under a nitrogen atmosphere. After cooling of thesolution to +5° C., 4.8 g (0.12 mol) of sodium hydroxide and 13.3 ml(0.12 mol) of 50% aqueous glyoxylic acid are added, and the reactionmixture is stirred at room temperature for 4 hours. After 4 hours each,another 0.12 mol of sodium hydroxide and glyoxylic acid (a total of 0.36mol) are added two more times. The reaction mixture is then additionallystirred for 12 hours, then neutralised with concentrated hydrochloricacid and washed twice with 75 ml of petroleum ether. The aqueous phaseis then acidified with concentrated hydrochloric acid and extractedseveral times with ether. The organic phases are combined, dried overmagnesium sulfate and concentrated on a vacuum rotary evaporator. Inthis manner, the following products are obtained:3,5-dimethyl-4-hydroxymandelic acid, melting point 132°-135° C., yield85%; 4 -hydroxy-3-methylmandelic acid, melting point 115°-120° C., yield55%; 4-hydroxy-3-tert-butylmandelic acid, melting point 156°-158° C.,yield 26%; 3-isopropyl-4-hydroxy-2-methylmandelic acid, melting point114°-119° C., yield 20%; 3,5-di-tert-butyl-4-hydroxymandelic acid,melting point 177°-180° C., yield 45%; and3-methyl-5-tert-butyl-4-hydroxymandelic acid, melting point 138°-141°C., yield 50%.

EXAMPLE 3 Preparation of3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one(Compound (109), Table 1).

53.6 g (0.53 mol) of acetic anhydride are added dropwise over a periodof about 10 minutes to a suspension of 183.3 g (0.50 mol) of3-(3,5-dimethyl-4-hydroxyphenyl)-5,7-di-tert-butylbenzofuran-2-one(compound (107), Table 1, Example 2) in 250 ml of xylene and 0.5 ml (7.7mmol) of methanesulfonic acid which is stirred at 105° C. under anitrogen atmosphere. The clear, colourless reaction mixture isconcentrated at about 170° C. under a slight vacuum. 500 ml of 1-butanolare carefully added to the residue and the mixture is cooled withice/water. The precipitated product is filtered and washed with 100 mlof 1-butanol. Drying gives 197.6 g (97%) of3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one,melting point 165°-166° C. (compound (109), Table 1).

Compound (120) is prepared from compound (101) and compound (133) fromcompound (131) analogously to Example 3.

EXAMPLE 4 Preparation of3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one(Compound (110), Table 1)

180.1 g (1.49 mol) of pivaloyl chloride are added dropwise over a periodof 25 minutes to a suspension of 274.5 g (0.75 mol) of3-(3,5-dimethyl-4-hydroxyphenyl)-5,7-di-tert-butylbenzofuran-2-one,(compound (107), Table 1, Example 2) in 600 ml of xylene and 7.5 ml(115.7 mmol) of methanesulfonic acid which is stirred at 95° C. under anitrogen atmosphere. The clear, homogeneous reaction mixture is thenrefluxed for another 2.5 hours and then concentrated under a slightvacuum. 50 ml of 1-butanol and 600 ml of methanol are carefully pouredinto the liquid, hot residue at about 170° C. through the condenser andthe mixture is cooled with ice/water. The precipitated product isfiltered and washed with 350 ml of cold methanol. Drying gives 311.9 g(92%) of3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one,melting point 140°-142° C. (compound (110 ), Table 1).

The compounds (111), (112), (113), (114), (115), (117), (118), (119),(121), (122), (123), (124), (125) and (129) are prepared from thecorresponding phenols and acid halides analogously to Example 4.

EXAMPLE 5 Preparation of3,3'-bis[3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one](Compound (127), Table 1)

18.02 g (40 mmol) of3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one(compound (110), Example 4) are added under a nitrogen atmosphere to asodium ethoxide solution prepared by addition of 0.92 g (40 mmol) ofsodium to 80 ml of absolute ethanol. A solution of 5.08 g (20 mmol) ofiodine in 50 ml of diethyl ether is then added dropwise at roomtemperature over a period of about 10 minutes. The reaction mixture isthen additionally stirred for 5 minutes, 1.0 g (5.3 mmol) of sodiumpyrosulfite is then added, and the mixture is diluted with 400 ml ofwater. The precipitate formed is extracted with methylene chloride. Theorganic phases are separated off, washed with water, combined, driedover sodium sulfate and concentrated on a vacuum rotary evaporator.Crystallisation of the residue from ethanol/methylene chloride gives16.8 g (93%) of the3,3'-bis[3(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one],melting point 268°-270° C. (compound (127), Table 1).

                                      TABLE 1                                     __________________________________________________________________________                                      m.p. C (%), H (%)                                                                            Yield                        No.                                                                              Compound                       (°C.)                                                                       (calculated/found)                                                                      (%)                          __________________________________________________________________________    101                                                                               ##STR24##                     187-190                                                                            78.07 78.04                                                                        7.74 7.84                                                                          57                           102                                                                               ##STR25##                     180-183                                                                            78.38 78.26                                                                        8.01 8.02                                                                          55                           103                                                                               ##STR26##                     191-201 (dcmp.)                                                                     ##STR27##                                                                              67                           104                                                                               ##STR28##                     186-189                                                                            79.15 79.11                                                                        8.69 8.91                                                                          54                           105                                                                               ##STR29##                     186-189                                                                            77.39 77.36                                                                        7.14 7.18                                                                          54                           106                                                                               ##STR30##                     211-215                                                                            77.75 77.82                                                                        7.46 7.47                                                                          65                           107                                                                               ##STR31##                     225-228                                                                             78.65 78.68                                                                       8.25 8.38                                                                          88                           108                                                                               ##STR32##                     oil                                                                                 ##STR33##                                                                              46                           109                                                                               ##STR34##                     165-166                                                                            76.44 76.37                                                                        7.90 7.91                                                                          97                           110                                                                               ##STR35##                     140-142                                                                            77.30 77.34                                                                        8.50 8.72                                                                          92                           111                                                                               ##STR36##                     resin.sup.a)                                                                       78.01 77.90                                                                        9.00 9.01                                                                          95                           112                                                                               ##STR37##                     resin                                                                              78.42 78.28                                                                        9.29 9.27                                                                          96                           113                                                                               ##STR38##                     oil                                                                                 ##STR39##                                                                              87                           114                                                                               ##STR40##                     oil                                                                                 ##STR41##                                                                              58                           115                                                                               ##STR42##                     142-145                                                                            73.95 73.92                                                                         7.81 8.01                                                                         45                           116                                                                               ##STR43##                     175-189                                                                            72.23 72.56                                                                        6.85 7.13                                                                          30                           117                                                                               ##STR44##                     119-121                                                                            76.11 76.21                                                                        7.67 7.59                                                                          82                           118                                                                               ##STR45##                     143-145                                                                            76.44 76.65                                                                        7.90 7.85                                                                          79                           119                                                                               ##STR46##                     oil                                                                                 ##STR47##                                                                              70                           120                                                                               ##STR48##                     163-165                                                                            75.76 75.74                                                                        7.42 7.49                                                                          85                           121                                                                               ##STR49##                     136-142                                                                            76.74 76.77                                                                        8.11 8.31                                                                          73                           122                                                                               ##STR50##                     147-149                                                                            77.21 77.60                                                                        9.07 8.97                                                                          65                           123                                                                               ##STR51##                     188-190                                                                             ##STR52##                                                                              59                           124                                                                               ##STR53##                     130-135                                                                            77.39 77.20                                                                        7.89 8.07                                                                          33                           125                                                                               ##STR54##                     168-179                                                                             ##STR55##                                                                              25                           126                                                                               ##STR56##                     158-164                                                                            71.82 71.38                                                                        5.67 5.74                                                                            16.5                       127                                                                               ##STR57##                     268-270                                                                            77.47 77.49                                                                        8.30 8.38                                                                          93                           128                                                                               ##STR58##                     221-226                                                                            71.10 70.90                                                                        5.22 5.33                                                                          15                           129                                                                               ##STR59##                     146-150                                                                            71.21 71.22                                                                        6.90 6.98                                                                          59                           130                                                                               ##STR60##                     157-160                                                                            74.97 74.92                                                                        7.66 7.72                                                                          50                           131                                                                               ##STR61##                     215-222 (dcmp.)                                                                    79.37 79.16                                                                        8.88 8.97                                                                          88                           132                                                                               ##STR62##                     173-175                                                                            79.96 79.77                                                                        9.77 9.41                                                                          21                           133                                                                               ##STR63##                     resin                                                                              77.30 77.04                                                                        8.50 8.49                                                                          74                           134                                                                               ##STR64##                     221-226                                                                            71.10 70.90                                                                        5.22 5.33                                                                          15                           __________________________________________________________________________     .sup.a) The octanoic acid used is a mixture of isomers                   

EXAMPLE 6 Stabilisation of Polypropylene in Multiple Extrusion

1.3 kg of polypropylene powder (Profax 6501) prestabilised with 0.025%of Irganox® 1076 (n-octadecyl3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionate) (at a melt index of 3.2measured at 230° C. and on 2.16 kg) are mixed with 0.05% of Irganox®1010 (pentaerythritoltetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 0.05% ofcalcium stearate, 0.03% of dihydrotalcite (DHT 4A®, Kyowa ChemicalIndustry Co., Ltd., [Mg₄.5 Al₂ (OH)₁₃ CO₃.3.5H₂ O]) and 0.015% of thecompound from Table 1. This mixture is extruded in an extruder ofcylinder diameter 20 mm and length 400 mm at 100 revolutions per minute,the 3 heating zones being set at the following temperatures: 260° C.,270° C. and 280° C. The extrudate is cooled by passing it through awaterbath and then granulated. These granules are repeatedly extruded.After 3 extrusions, the melt index is measured (at 230° C. on 2.16 kg).A large increase in the melt index indicates substantial chaindegradation, i.e. poor stabilisation. The results are summarised inTable 2.

                  TABLE 2                                                         ______________________________________                                        Compound from  Melt index                                                     Table 1        after 3 extrusions                                             ______________________________________                                        --             20.0                                                           110            6.4                                                            112            6.7                                                            117            5.7                                                            118            5.7                                                            119            6.7                                                            121            5.8                                                            122            6.0                                                            ______________________________________                                    

EXAMPLE 7 Stabilisation of Polyethylene During Processing

100 parts of polyethylene powder (Lupolen® 5260 Z) are mixed with 0.05part of pentaerythritoltetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 0.05 part oftris(2,4-di-tert-butylphenyl) phosphite and 0.05 part of the compoundfrom Table 1, and the mixture is kneaded at 220° C. and 50 revolutionsper minute in a Brabender Plastograph. During this time, the resistanceto kneading is continuously recorded as torque. During the kneadingtime, the polymer, after remaining constant for an extended period oftime, begins to crosslink, which can be detected by a rapid increase intorque. In Table 3, the time until the substantial increase in torque isobserved is given as a measure of stabiliser effect. The longer thistime, the better the stabiliser effect.

                  TABLE 3                                                         ______________________________________                                        Compound from  Time until torque                                              Table 1        increases (min)                                                ______________________________________                                        --              9.0                                                           110            18.0                                                           112            16.5                                                           117            21.0                                                           118            18.5                                                           119            19.0                                                           121            23.0                                                           122            19.0                                                           ______________________________________                                    

EXAMPLE 8 Stabilisation of Thermoplastic Styrene-based Elastomers

70 g of styrene/butadiene/styrene (SBS, ®Finapren 416) are kneadedtogether with 0.25% of the stabiliser to be tested from Table 1 in aBrabender Plastograph at 200° C. and 60 revolutions per minute for 30minutes. The induction time, i.e. the kneading time in minutes untiltorque increases by 1 Nm after the torque minimum, is determined fromthe shape of the torque curve. A large increase in induction timeindicates good stabilisation. The results are summarised in Table 4.

                  TABLE 4                                                         ______________________________________                                        Compound from   Induction time                                                Table 1         in minutes                                                    ______________________________________                                        --               5.0                                                          109             12.1                                                          110             12.0                                                          ______________________________________                                    

EXAMPLE 9 Stabilisation of Polybutadiene Rubber

70 g of polymer (Buna CB 529 C) are kneaded together with 0.25% of thestabiliser to be tested from Table 1 in a Brabender Plastograph at 160°C. and 60 revolutions per minute for 30 minutes. The induction time,i.e. the kneading time in minutes until torque increases by 1 Nm afterthe torque minimum, is determined from the shape of the torque curve. Alarge increase in induction time indicates good stabilisation. Theresults are summarised in Table 5.

                  TABLE 5                                                         ______________________________________                                        Compound from   Induction time                                                Table 1         in minutes                                                    ______________________________________                                        --               4.0                                                          107             127.5                                                         ______________________________________                                    

EXAMPLE 10 Stabilisation of a Polyether/polyurethane Flexible Foam

470 mg (0.3%, relative to the polyol) of a stabiliser mixture accordingto the invention (Table 6) are dissolved in 157 g of an antioxidant-freepolyether polyol, ®Lupranol 2045, (trifunctional polyether polyol havingprimary hydroxyl groups; hydroxyl number 35 mg of KOH/g, water contentbelow 0.1%, acid number below 0.1 mg of KOH/g). 10.24 g of a solution of1.74 g of ®TECOSTAB [polysilicone from Goldschmidt, GER], 0.48 g ofdiazabicyclooctane [amine catalyst] and 0.8 g of water are added to thesolution, and the mixture is vigorously stirred at 100 rpm for 60seconds. 3.2 g of a solution of 0.32 g of tin octoate (catalyst) in 2.9g of the above polyol are then added, and the mixture is againvigorously stirred at 100 rpm for 60 seconds. This is immediatelyfollowed by addition of 98 g of an isocyanate (®Lupranat T80 BASF; amixture of 2,4 - and 2,6-toluylene diisocyanate) with vigorous stirring,and, after 6 seconds, the mixture is poured into a lined mould. Theexothermal temperature during foaming to give a foam block is measured.The foam blocks are cooled and stored at 5° C. in a conditioning cabinetfor 24 hours. 2 cm thick discs are sawed off the centre of the blocksand from these round (cylindrical) test specimens are cut out by meansof a drilling tool. The specimens are aged in a test tube with admissionof air at 190° C. in a preheated aluminium block thermostat. Yellowingof these specimens is determined in accordance with ASTM D-1925 asYellowness Index (YI). The later yellowing takes place and the smallerthe Yellowness Index, the better the stabilisation. The results aresummarised in Table 6.

                                      TABLE 6                                     __________________________________________________________________________              Yellowness Index after oven ageing (0 to 160 min)                   Stabiliser mixture                                                                      0   10  20  30 40 60 80 100                                                                              120                                                                              140                                                                              160                                __________________________________________________________________________    --        -0.7                                                                              44  48  55 57 62                                                0.24% of comp. 109                                                                      -2  0   1.8 2.1                                                                              2.8                                                                              4.4                                                                              7.4                                                                              19 27 28 36                                 plus 0.06% of AO1                                                             0.24% of comp. 109                                                                      -2  -0.3                                                                              0.2 0.5                                                                              1.3                                                                              2.9                                                                              4  15 28 30 38                                 plus 0.06% of AO2                                                             0.24% of comp. 109                                                                      -1.9                                                                              -0.7                                                                              -0.2                                                                              1.3                                                                              1.7                                                                              3.9                                                                              12 28 34 36 43                                 plus 0.06% of AO3                                                             __________________________________________________________________________     AO1 is a mixture of polyalkylated diphenylamines (® Irganox 5057)         AO2 is 4,4'-thiobis(6tert-butyl-3-methylphenol)(® Santonox R)             AO3 is 2,2'-methylenebis(6tert-butyl-4-methylphenol)                     

What is claimed is:
 1. A composition comprisinga) an organic materialwhich is subject to oxidative, thermal or light-induced degradation andb) at least one compound of the formula(1) ##STR65## in which R₂, R₃, R₄and R₅, independently of one another, are hydrogen. C₁ -C₂₅ alkyl, C₇-C₉ phenylalkyl, unsubstituted or C₁ -C₄ alkyl-substituted phenyl,unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₈ cycloalkyl; C₁ -C₁₈alkoxy, hydroxyl, C₁ -C₂₅ alkanoyloxy, C₃ -C₂₅ alkenoyloxy, C₃ -C₂₅alkanoyloxy which is interrupted by oxygen, sulfur or >N--R₁₆ ; C₆ -C₉cycloalkylcarbonyloxy, benzoyloxy or C₁ -C₁₂ alkyl-substitutedbenzoyloxy, where R₁₆ is hydrogen or C₁ -C₈ alkyl, or, furthermore, theradicals R₂ and R₃ or the radicals R₄ and R₅ together with the carbonatoms to which they are bound form a phenyl ring, R₄ is additionally--(CH₂)_(n) --COR₁₁, in which n is 0, 1 or 2, R₁₁ is hydroxyl, ##EQU4##C₁ -C₁₈ alkoxy or ##STR66## R₁₄ and R₁₅, independently of one another,are hydrogen or C₁ -C₁₈ alkyl, M is an r-valent metal cation and r is 1,2 or 3, R₇, R₈, R₉ and R₁₀, independently of one another, are hydrogen,C₁ -C₄ alkyl or C₁ -C₄ alkoxy, with the proviso that at least one of theradicals R₇, R₈, R₉ and R₁₀ is hydrogen and, in the case where R₃, R₅,R₆, R₇ and R₁₀ are hydrogen, R₄ is additionally a radical of the formula(2) ##STR67## in which R₂, R₈ and R₉ are as defined above and R₁ is asdefined below for m=1, and R₁₂ and R₁₃, independently of one another,are hydrogen, C₁ -C₁₂ alkyl or phenyl, m is 1 or 2, and, in the casewhere m is 1, R₁ is hydrogen, C₁ -C₂₅ alkanoyl, C₃ -C₂₅ alkenoyl, C₃-C₂₅ alkanoyl which is interrupted by oxygen, sulfur or >N--R₁₆ ; C₆ -C₉cycloalkylcarbonyl, benzoyl or C₁ -C₁₂ alkyl-substituted benzoyl, R₁₆ isas defined above and R₆ is hydrogen or a radical of the formula (3)##STR68## in which R₁, R₂, R₃, R₄, R₅, R₇, R₈, R₉ and R₁₀ are as definedabove, and, in the case where m is 2, R₁ is ##STR69## in which R₁₇ is adirect bond, C₁ -C₁₈ alkylene, C₂ -C₁₈ alkylene which is interrupted byoxygen, sulfur or >N--R₁₆ ; C₂ -C₁₈ alkenylene, C₂ -C₂₀ alkylidene, C₇-C₂₀ phenylalkylidene, C₅ -C₈ cycloalkylene, C₇ -C₈ bicycloalkylene orphenylene, R₁₆ is as defined above and R₆ is hydrogen.
 2. A compositionaccording to claim 1, in which R₂, R₃, R₄ and R₅, independently of oneanother, are hydrogen C₁ -C₁₈ alkyl, benzyl, phenyl, C₅ -C₈ cycloalkyl,C₁ -C₈ alkoxy, hydroxyl, C₁ -C₁₈ alkanoyloxy, C₃ -C₁₈ alkenoyloxy orbenzoyloxy, R₄ is additionally --(CH₂)_(n) --COR₁₁, and, in the casewhere m is 1, R₁ is hydrogen, C₁ -C₁₈ alkanoyl, C₃ -C₁₈ alkenoyl, C₃-C₁₈ alkanoyl which is interrupted by oxygen, sulfur or >N--R₁₆ ; C₆ -C₉cycloalkylcarbonyl, benzoyl or C₁ -C₈ alkyl-substituted benzoyl, R₁₆ isas defined above and, in the case where m is 2, R₁ is ##STR70## in whichR₁₇ is a direct bond, C₁ -C₁₂ alkylene, C₂ -C₁₂ alkylene which isinterrupted by oxygen, sulfur or >N--R₁₆ ; C₂ -C₁₂ alkenylene, C₂ -C₁₂alkylidene, C₇ -C₁₂ phenylalkylidene, C₅ -C₈ cycloalkylene or phenyleneand R₁₆ is as defined above.
 3. A composition according to claim 1, inwhich at least two of the radicals R₂, R₃, R₄ and R₅ are hydrogen.
 4. Acomposition according to claim 3, in which R₃ and R₅ are hydrogen.
 5. Acomposition according to claim 1, in which R₃, R₅, R₇ and R₁₀,independently of one another, are hydrogen or C₁ -C₄ alkyl, R₂ ishydrogen or C₁ -C₁₈ alkyl, R₄ is hydrogen, C₁ -C₁₂ alkyl, C₁ -C₈ alkoxy,hydroxyl or --(CH₂)_(n) --COR₁₁, in which n is 0, 1 or 2, R₁₁ ishydroxyl or C₁ -C₁₂ alkoxy, and, in the case where m is 1, R₁ ishydrogen, C₁ -C₁₈ alkanoyl, C₃ -C₁₈ alkanoyl which is interrupted byoxygen; or C₃ -C₁₈ alkenoyl, and, in the case where m is 2, R₁ is##STR71## in which R₁₇ is C₁ -C₈ alkylene, C₂ -C₈ alkenylene, C₂ -C₈alkylidene, C₇ -C₉ phenylalkylidene, cyclohexylene or phenylene.
 6. Acomposition according to claim 1, in which R₂ is hydrogen or C₁ -C₁₄alkyl, R₃ and R₅ are hydrogen, R₄ is hydrogen, hydroxyl, C₁ -C₄ alkyl,C₁ -C₄ alkoxy or --(CH₂)_(n) --COR₁₁, in which n is 2 and R₁₁ ishydroxyl, R₇, R₈, R₉ and R₁₀, independently of one another, arehydrogen, C₁ -C₄ alkyl or C₁ -C₄ alkoxy, with the proviso that at leastone of the radicals R₇, R₈, R₉ or R₁₀ is hydrogen, m is 1 and R₁ ishydrogen, C₁ -C₁₈ alkanoyl, C₃ -C₈ alkanoyl which is interrupted byoxygen; or is C₃ -C₄ alkenoyl and R₆ is hydrogen or a radical of theformula (3) ##STR72## in which R₁, R₂, R₃, R₄, R₅, R₇, R₈, R₉ and R₁₀are as defined above.
 7. A composition according to claim 1, in which R₂is hydrogen or C₁ -C₁₄ alkyl, R₃, R₅, R₆, R₇ and R₁₀ are hydrogen, R₄ ishydrogen or C₁ -C₄ alkyl, R₈ and R₉, independently of one another, arehydrogen, C₁ -C₄ alkyl or C₁ -C₄ alkoxy, m is 1 and R₁ is C₁ -C₁₀alkanoyl or C₃ -C₄ alkenoyl.
 8. A composition according to claim 1, inwhich component a) is a synthetic polymer.
 9. A composition according toclaim 1, in which component b) is present in an amount of 0.0005 to 5%,relative to the weight of component a).
 10. A composition according toclaim 1, additionally containing an organic phosphite or phosphonite.11. A process for the stabilisation of an organic material againstoxidative, thermal or light-induced degradation, which comprisesincorporating therein or applying thereto at least one compound of theformula (1) defined in claim 1.